(3R,4S)-4-benzyloxy-tetrahydrothiophene-3-carboxylic (1S)-camphorsultam amide | 252192-75-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3R,4S)-4-benzyloxy-tetrahydrothiophene-3-carboxylic (1S)-camphorsultam amide
• 英文别名: [(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-[(3R,4S)-4-phenylmethoxythiolan-3-yl]methanone；[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-[(3R,4S)-4-phenylmethoxythiolan-3-yl]methanone
• CAS: 252192-75-9
• 化学式: C₂₂H₂₉NO₄S₂
• 分子量: 435.609
• InChiKey: MUYDKOJGSQWQOU-ACMVSEJYSA-N

物化性质

• 沸点：
  579.0±60.0 °C(predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S)-4-benzyloxy-tetrahydrothiophene-3-carboxylic (1S)-camphorsultam amide 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 18-冠醚-6 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 59.0h， 生成 1-((3R,4R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrothiophen-3-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of 4′-thionucleosides by 1,3-dipolar cycloadditions of the simplest thiocarbonyl ylide with alkenes bearing electron-withdrawing groups

  摘要：

  Reactions of the simplest thiocarbonyl ylide with a variety of appropriate alkenes bearing electron-withdrawing substituents afforded the corresponding tetrahydrothiophenes, which could be easily elaborated into hydroxy and hydroxymethyl derivatives and then coupled with nucleobases to produce different 4 '-thionucleo sides. Particularly, alpha- and beta-anomers of 1-[3,4-bis(hydroxymethyl)tetrahydro-2-thienyl]-thymine, -cytosine, -uracil and -fluorouracil were prepared with dimethyl fumarate and maleate, while 1-[4-(hydroxymethyl)tetrahydro-2-thienyl]- and 1-[4-(hydroxymethyl)tetrahydro-3-thienyl]-thymine, -cytosine, -uracil and -fluorouracil were prepared with a chiral alpha,beta-unsaturated amide. These processes, simple in the experimental conditions and large availability of the starting materials, affording moderate to good yields of 4 '-thionucleosides, represent an optimum alternative to those, already known, based on sugars, which often have the drawbacks of a higher number of steps and lower yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.080
• 作为产物：
  描述：

  (E)-3-benzyloxypropenoyl chloride 在 甲基溴化镁 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 73.5h， 生成 (3R,4S)-4-benzyloxy-tetrahydrothiophene-3-carboxylic (1S)-camphorsultam amide
  参考文献：
  名称：

  Enantiomerically Pure trans-3,4-Disubstituted Tetrahydrothiophenes from Diastereoselective Thiocarbonyl Ylide Addition to Chiral α,β-Unsaturated Amides

  摘要：

  [GRAPHICS]Asymmetric 1,3-dipolar cycloadditions of a sulfur-containing 1,3-dipole and alpha,beta-unsaturated camphorsultam amides as dipolarophiles are described. The cycloaddition products, trans-3,4-disubstituted tetrahydrothiophenes, were obtained in high diastereomeric ratios (up to 90:10) and in high yields. Chromatographic removal of the minor diastereomer followed by cleavage of the chiral auxiliary furnished either the enantiomerically pure corresponding alcohol or carboxylic acid.

  DOI：

  10.1021/ol9910565

文献信息

• Synthesis of butenolides recently isolated from marine microorganisms
  作者：Staffan Karlsson、Fredrik Andersson、Palle Breistein、Erik Hedenström

  DOI：10.1016/j.tetlet.2007.08.123

  日期：2007.10

  The syntheses and 13C NMR analyses of four diastereomeric butenolides, two of which were recently isolated from the marine microorganisms Streptomycete B 5632 and Streptoverticillium luteoverticillatum 11014 are described. The two isolated butenolides were found to be one of the two diastereomers (4S,10R∗,11R∗)-4,11-dihydroxy-10-methyl-dodec-2-en-1,4-olide (RRS-1 or SSS-1) and one of the two diastereomers

  描述了四种非对映异构的丁烯内酯的合成和13 C NMR分析，其中最近从海洋微生物Streptomycete B 5632和leptoverticillium luteoverticillatum 11014中分离了其中的两种。两个分离的丁烯羟酸内酯被认为是两个非对映体中的一个（4小号，10 - [R * ，11 - [R * ）-4,11-二羟基-10-甲基十二碳-2-烯-1,4-内酯（RRS - 1或SSS - 1）和两个非对映异构体之一（4 S，10 S ∗，11 R ∗）-4,11-二羟基-10-甲基-十二烷基-2-烯-1,4-乙交酯（SRS - 1或RSS - 1）。硫代羰基内酯的不对称1,3-偶极环加成与连接到樟脑的双极亲和体和锂化的二噻吩对映体纯的乙烯基环氧乙烷的开环是构建三个立体中心的关键步骤。包括闭环复分解和Mitsunobu反演在内的进一步研究提供了四种非对映异构丁烯内酯。
• Enantiomerically Pure <i>trans</i>-3,4-Disubstituted Tetrahydrothiophenes from Diastereoselective Thiocarbonyl Ylide Addition to Chiral α,β-Unsaturated Amides
  作者：Staffan Karlsson、Hans-Erik Högberg

  DOI：10.1021/ol9910565

  日期：1999.11.1

  [GRAPHICS]Asymmetric 1,3-dipolar cycloadditions of a sulfur-containing 1,3-dipole and alpha,beta-unsaturated camphorsultam amides as dipolarophiles are described. The cycloaddition products, trans-3,4-disubstituted tetrahydrothiophenes, were obtained in high diastereomeric ratios (up to 90:10) and in high yields. Chromatographic removal of the minor diastereomer followed by cleavage of the chiral auxiliary furnished either the enantiomerically pure corresponding alcohol or carboxylic acid.
• Synthesis of 4′-thionucleosides by 1,3-dipolar cycloadditions of the simplest thiocarbonyl ylide with alkenes bearing electron-withdrawing groups
  作者：Antonino Corsaro、Venerando Pistarà、Maria Assunta Chiacchio、Elisa Vittorino、Roberto Romeo

  DOI：10.1016/j.tetlet.2007.05.080

  日期：2007.7

  Reactions of the simplest thiocarbonyl ylide with a variety of appropriate alkenes bearing electron-withdrawing substituents afforded the corresponding tetrahydrothiophenes, which could be easily elaborated into hydroxy and hydroxymethyl derivatives and then coupled with nucleobases to produce different 4 '-thionucleo sides. Particularly, alpha- and beta-anomers of 1-[3,4-bis(hydroxymethyl)tetrahydro-2-thienyl]-thymine, -cytosine, -uracil and -fluorouracil were prepared with dimethyl fumarate and maleate, while 1-[4-(hydroxymethyl)tetrahydro-2-thienyl]- and 1-[4-(hydroxymethyl)tetrahydro-3-thienyl]-thymine, -cytosine, -uracil and -fluorouracil were prepared with a chiral alpha,beta-unsaturated amide. These processes, simple in the experimental conditions and large availability of the starting materials, affording moderate to good yields of 4 '-thionucleosides, represent an optimum alternative to those, already known, based on sugars, which often have the drawbacks of a higher number of steps and lower yields. (c) 2007 Elsevier Ltd. All rights reserved.